A Silver‐Catalyzed Spirocyclization of Alkynyl Silyl Enol Ethers
作者： Christian Schäfer , Michel Miesch , Laurence Miesch
关键词: Medicinal chemistry 、 Catalysis 、 Homogeneous catalysis 、 Ring (chemistry) 、 Chemistry 、 Enol 、 Bicyclic molecule 、 Silylation 、 Iodide 、 Organic chemistry 、 Cycloisomerization
摘要: Ring out the old: The cycloisomerization of alkynyl silyl enol ethers proceeds at ambient temperature under mild conditions silver catalysis. Mono- or bicyclic spiro compounds can be obtained by 5-exo-dig reactions. Trapping vinyl species with an iodide source, such as N-iodosuccinimide (NIS), afforded alkenyl derivatives.
sci-hub.se 参考文章(41)
Hsien-Hsun Lin, Wen-Sheng Chang, Shun-Yuan Luo, Chin-Kang Sha, Photoinduced Atom-Transfer Cyclization of α-Iodocycloalkanones Bearing an Allenyl Side Chain Organic Letters. ,vol. 6, pp. 3289- 3292 ,(2004) , 10.1021/OL048822E
Yoshinori Yamamoto, From σ- to π-Electrophilic Lewis Acids. Application to Selective Organic Transformations Journal of Organic Chemistry. ,vol. 72, pp. 7817- 7831 ,(2007) , 10.1021/JO070579K
H. V. Rasika Dias, Carl J. Lovely, Carbonyl and olefin adducts of coinage metals supported by poly(pyrazolyl)borate and poly(pyrazolyl)alkane ligands and silver mediated atom transfer reactions. Chemical Reviews. ,vol. 108, pp. 3223- 3238 ,(2008) , 10.1021/CR078362D
Nicolas Mézailles, Louis Ricard, Fabien Gagosz, Phosphine gold(I) bis-(trifluoromethanesulfonyl)imidate complexes as new highly efficient and air-stable catalysts for the cycloisomerization of enynes. Organic Letters. ,vol. 7, pp. 4133- 4136 ,(2005) , 10.1021/OL0515917
Míriam Álvarez-Corral, Manuel Muñoz-Dorado, Ignacio Rodríguez-García, Silver-mediated synthesis of heterocycles. Chemical Reviews. ,vol. 108, pp. 3174- 3198 ,(2008) , 10.1021/CR078361L
J. M. CONIA, P. Le PERCHEC, The Thermal Cyclisation of Unsaturated Carbonyl Compounds Synthesis. ,vol. 1975, pp. 1- 19 ,(1975) , 10.1055/S-1975-23652
Andrea K. Buzas, Florin M. Istrate, Fabien Gagosz, Gold-catalyzed rearrangement of propargylic tert-butyl carbonates Tetrahedron. ,vol. 65, pp. 1889- 1901 ,(2009) , 10.1016/J.TET.2008.11.108
Nicolas Kern, Aurélien Blanc, Jean-Marc Weibel, Patrick Pale, Gold(i)-catalyzed rearrangement of aryl alkynylaziridines to spiro[isochroman-4,2′-pyrrolines] Chemical Communications. ,vol. 47, pp. 6665- 6667 ,(2011) , 10.1039/C1CC11351H
Louis Ricard, Fabien Gagosz, Synthesis and Reactivity of Air-Stable N-Heterocyclic Carbene Gold(I) Bis(trifluoromethanesulfonyl)imidate Complexes Organometallics. ,vol. 26, pp. 4704- 4707 ,(2007) , 10.1021/OM7006002
Sonia Montel, Didier Bouyssi, Geneviève Balme, An Efficient and General Microwave-Assisted Copper-Catalyzed Conia-Ene Reaction of Terminal and Internal Alkynes Tethered to a Wide Variety of Carbonucleophiles Advanced Synthesis & Catalysis. ,vol. 352, pp. 2315- 2320 ,(2010) , 10.1002/ADSC.201000351